American Chemical Society
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A Short Total Synthesis of (+)-Furanomycin

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journal contribution
posted on 2000-02-09, 00:00 authored by Michael Pete VanBrunt, Robert F. Standaert
Furanomycin is a Streptomyces metabolite that substitutes for isoleucine in protein translation. We report a concise and modular synthesis starting from the Garner aldehyde and proceeding in seven steps to furanomycin. The key steps include a stereoselective acetylide addition and the Ag+-mediated cyclization of an α-allenic alcohol to construct the trans-2,5-dihydrofuran. The efficiency (12% overall yield) and flexibility of the route will provide ample quantities of furanomycin and analogues for protein engineering.